Jessica

God, we hate it when this happens. New York hands their readers a woefully misguided fish in the sartorial barrel, and we are forced — yes, forced — to go to town on the poor soul who posed for their Look Book. This week, that person is Gloria Ward, a wig-wearing beautician who admits that on the day this photo was taken, she was looking "a little flashy." Indeed! Gloria is into fake eyelashes and a triple coat of mascara, paired with a disturbingly large blazer. You should also know that she was once a drummer in her husband's band, the Ink Spots, and she fell in love with her husband after he asked her if she did any typing. We suppose this makes Gloria a real romantic.

Honestly, we don't know what more to say. After the jump, Intern Alexis asks Karen Wilson, Kristin Meyer, and our own Henry the Intern to deal with Gloria's style.

Gloria has clearly embraced the hipster trends of leggings, cowboy boots and drumming. What other hipster accouterments (cultural or material) does she indulge in?

I sense from her outfit and her wild drumming ways that Gloria likes to go to rock shows where she gets really close to the stage and snaps digital photos of the band with the red eye flash turned on. Also, if she can throw an elbow into the rib of someone standing there, innocently listening to the music, she totally will. Then she goes home to flickr her sweet pics. I bet there's also a star tattoo somewhere underneath those leggings, probably on the inside of her ankle.

What's under the wig?

Her dreams, maybe. Or a really delicious snack.

What happened when Gloria's husband found out Gloria only did "very little typing"?

He realized his practice of finding stenographers by picking them up in bars was no longer going to be an effective hiring practice. Now he uses Craigslist; it's much easier and the pool of applicants don't insist upon joining your famous band as "the drummer."

What, if anything, would you change about Gloria's style?

I know that post-Diane Keaton in Something's Gotta Give, women of a certain age have openly embraced the turtleneck. I say, Gloria, step away from that abyss. Sweater up to the neck plus collared shirt plus sweater on top of that? This is layered look even American Apparel would disavow. I'm all for warmth and whatnot, but seriously. You say you're a conservative dresser but those distressed cowboy boots scream otherwise. Embrace that, girl.

Kristin Meyer, Former Blogger "KikiNYC" and Aspiring Madame

Gloria has clearly embraced the hipster trends of leggings, cowboy boots and drumming. What other hipster accoutrements (cultural or material) does she indulge in?

From the neck down she reminds me of paper dolls I played with when I was four that you could mix and match their accessories, and seeing as how that was 1984... that would be about right. If Markie Post was the hipster of her day (and I believe Night Court proved that), than I'm thinking the neckercheif, shoulder pads, and oversized Coca-Cola button-down all add as further proof that Gloria is ahead of the curve.

What's under the wig?

I'm thinking 25 years worth of almost empty Annette 2 mascara tubes (approximately... 27,375 tubes), her "go-to" Caboodle, a sealed birth certificate to be opened upon her death, and the last surviving McRib she's been saving for a rough day.

What happened when Gloria's husband found out Gloria only did "very little typing"?

He told her to get those hands on his "QWERTY and prove it!"

What, if anything, would you change about Gloria's style?

Personally, not a thing. But as for Markie... she thinks Multiples (or Units as they were known in the Midwest) are so 1983. She'd suggest Gloria swap out the skirt for something she recently saw Roz the Baliff look smashing in.